


I Shouldn't Have Said That

by littlefirefly31



Series: Kink/Request Fics [5]
Category: Supernatural
Genre: Angst, Dom!Sam, Emotional Hurt/Comfort, Hurt!Sam, M/M, Misunderstandings, Wincest - Freeform, hurt!Dean
Language: English
Status: Completed
Published: 2014-06-03
Updated: 2014-06-03
Packaged: 2018-02-03 05:22:50
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 5,015
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1732682
Author URL: https://archiveofourown.org/users/littlefirefly31/pseuds/littlefirefly31
Summary: <blockquote class="userstuff">
              <p>Prompt: Preferably Pre-Stanford era or during Stanford. Virgin!Bottom!Dean/Top!Sam, Sam/OMC. Jealous, insecure Dean. Guilty, regretful Sam. Misunderstanding, Lots of angst, Hurt/Comfort.<br/>Dean's been pining after Sam for years and the guilt of his love has taken a great toll emotionally. Dean's breaking point is finding out Sam has a boyfriend who appears to be Sam's everything and when Dean confronts Sam about it out of hurt and betrayal, Sam misunderstands Dean's actions for homophobia and ugly words are said that tear Dean apart.</p>
            </blockquote>





	I Shouldn't Have Said That

**Author's Note:**

> Hope this fills your request!

Some days it felt like guilt was eating Dean alive. It was this horrible monster clawing at his heart and mocking him because Dean, the stupid bastard that he was, went and fell in love with his baby brother. Sam and his stupid dimples and hazel eyes and ridiculously floppy hair that made Dean’s heart flip-flop. Sam and his stupid 16-year-old body that had reacted quite nicely with puberty combined with John’s intense workouts.

Sam was Dean’s lifeline, his soul, his other half. Dean, who promised to take care of Sam under any and every circumstance, had committed the worst crime possible. Dean was terrified he’d let his secret out one day. Sam would look at him under his cute droopy bangs and flash his cute dimples and Dean would just be _gone_.

It didn’t help that they shared a room. Dean knew it was necessary because they couldn’t afford anything else. But Dean would stay awake for hours listening to Sam breathe and shift under his sheets. Sam didn’t sleep with a shirt on, and it really tested Dean’s self-control.

“Dean!” Sam slammed the door. “I’m home!”

Dean looked up from his position on the table. “You’re late?”

“I was with a friend.” Sam dropped his backpack on the ground and flopped on the bed. “How do you flirt, Dean?”  
Dean raised an eyebrow. “I breathe and girls fall over me. Flirting is just second nature.”  

“Okay, but for those of us who don’t have girls tripping over themselves to hook up, how do you flirt?” Sam looked at him eagerly.

“Why?” Dean smirked. “Got your eye on a pretty girl or something?”  
“Or something,” Sam muttered. “Tell meeee.”

“Fine, you little brat.” Dean didn’t want to tell Sam how to flirt. He wanted to lock Sam away and keep him for himself. But that would be too suspicious. “I guess when I want to flirt, I wink, I smile, buy her a drink. I try and make her laugh. Girls dig a guy who can make them laugh. Listen to what she’s saying and tell her she’s gorgeous. Girls eat up that flattery shit.”

“And what if a girl was flirting with you?” Sam blushed. “How would she flirt with you?”  
“I dunno, I like when girls look at me from under their hair. If they give me this big eye stare with just the tiniest hint of lust, I’m hooked. A nice smile is good too. Dimples are cute. If a girl smiles at me like I’m the moon, it makes me feel powerful.” Dean blushed slightly. He basically just described his baby brother.

Sam didn’t seem to have noticed. “So that’s how you flirt with a guy,” He mused.

Dean could tell that it wasn’t aimed at him. But curiosity got the better of him. “Why does flirting with a guy matter?” Sam was _his_. Flirting with a girl was one thing. But the only guy in Sam’s life was Dean, and that’s how it should always be.

“What does it matter to you? I just want to know how to flirt,” Sam snapped.

Dean raised his hands in defense. “I didn’t mean any harm.”

“Sorry.” Sam grabbed his backpack. “I’m gonna just… do my homework.”

Dean was still suspicious. “Well, if you need anything else, you know where to find me.”

“Yeah, I know.” A look of intense concentration settled over Sam’s face as he did his homework. Sam had a love of studying and reading that Dean could never fully understand. Dean was more comfortable behind a gun, but Sam’s best weapon was his clever mind. Dean knew that would get him far.

But he wasn’t selfless enough to let Sam get too far away from him. His kid brother could go to college and have that apple pie life for him. The same life that Sam had always dreamed of and Dean had secretly hoped Sam could have. But Dean would fight tooth and nail before his baby brother left him.

*

“I’m going out tonight,” Sam announced.

“Yeah?” Dean looked up from cleaning the gun. “And who says I’m gonna let you?”  
Sam glared. “I do. I’m 16. And I’m not satisfied to sitting around here, cleaning guns, and waiting on Dad to come back. I’m going out.”

“It’s a school night,” Dean pointed out.

“I’ll be back early,” Sam countered. “And my homework’s done.”

Dean knew he had to pick his battles carefully, and this wasn’t one worth fighting. “Bring your phone. And if you don’t answer when I call or text, I’m hunting your ass down. Understand?”  
Sam mock-saluted. “’Course I do. I’m a good little _soldier_.”

The comment stung a little bit. Sam was always watched scathingly if Dad praised Dean for following orders. A compliment to Dean was an insult to Sam. But it’s not like Dean received a whole lot of praise from anyone these days.

“What time will you be home?” Dean asked.

“I dunno.”  
“Well _find out_.” Dean picked up the gun. “Your curfew’s one am. Be home.”

Sam opened his mouth like he was going to protest, but only slammed the door behind him as he left. Dean slumped in his seat, the clean gun scattered in pieces next to him.

*

Sam came home before his curfew. It was around 12:30 am that the younger Winchester stumbled into the room, giggling and leaning on the wall. Dean’s big brother instincts kicked in when he smelled the familiar scent of alcohol on his brother. “Are you fucking _drunk_?”  
“Buzzed,” Sam slurred. “Jus’ a coupla beers. Nothing-,” He hiccupped, “-bad.”

“You are _16 years old_ ,” Dean gritted. “I don’t know who told you it was okay to get drunk on a school night, but I’m gonna find them and kick their fucking ass.”

“Don’ kick James ass.” Sam fell face first onto his bed. “He’s kinda pretty.” He started to snore but Dean’s anger flared. This _James_ had pushed alcohol into his baby brother on a Wednesday night. For Christ’s sake—it was _Dean’s_ job to give Sam his first beer. _Dean_ would be the one laughing at his drunk little brother and giving him aspirin in the morning. This James character was in for a hell of a ass kicking.

*

Sam’s alarm was supposed to go off at 6:00 so he’d have time to get ready for school. Dean turned it off. He could write the principal a note saying that Sam was sick, and they’d only be in town for a week or so more anyways. One absence wouldn’t hurt.

It felt creepy at first, but Dean spent an hour just watching Sam. He’d spent too many mornings watching Sam sleep to be worried about it for more than a few minutes. He was Sam’s protector, and if Sam looked adorable and slightly fuckable when he was asleep—well, that was just a bonus.

There was McDonald’s a few blocks away. Around 11 Dean drove to pick them up a few breakfast sandwiches, a coffee for Dean, and an orange juice for Sam. He ate his food while keeping one eye focused on Sam.

It wasn’t until noon that Sam blearily blinked awake. “D’n?”

“Hey, sleepyhead.” Dean grinned. “How’s your head?”  
Sam winced. “It hurts. Real bad.” He flung a hand across his mouth. “Shit.” Sam tripped over his feet to get to the bathroom and barely got inside before Dean heard the sound of retching.

“First hangover?” Dean shouted. “How’s it feel?”  
“Fucker, talk quietly!”

“Aw, poor Sammy. You got drunk, now handle the consequences.” Dean sipped his coffee calmly. Dean didn’t like seeing Sammy in pain, but Sam went and got drunk with some other guy. This pain was Sam’s fault, and he’d deal with it. Alone.

Oh, who was Dean kidding?

Dean looked in the first aid kit for a bottle of painkillers and brought them and the orange juice into the bathroom. “Take these. And drink the juice slowly. Orange juice always makes me feel better. And it helps with the awful taste in your mouth, too.” Sam smiled gratefully up at Dean. Dean pretended he didn’t wish there was more than gratitude in that smile.

He wasn’t particularly successful.

“I have breakfast out here when you’re done puking,” Dean grunted. “Food will make you feel better.” He turned on his heel out of the bathroom before he did something stupid like demand to know who James is. And why Sam thought it was okay to get drunk with a stranger.

Sam trudged out of the bathroom with his lips sucking at the straw. Dean’s dick twitched and he put his legs under the table to prevent Sam from knowing what other uses Dean was imagining for Sam’s lips. “Eat up.”

It was quiet between them. Dean and Sam shared many quiet meals, but none of them had the crackle of tension in the air like this one did. Finally Dean blurted, “Who is he?”

“Who’s who?”

“James,” Dean sneered.

Sam raised an eyebrow. “A friend.”   
“A friend who got you drunk and let you walk home?”  
“He drove me, jackass,” Sam snapped. “And he’s a good friend. We study together. He’s the first friend I’ve made at this school, and I really like him.”

“If you ever come home drunk again, I’m calling Dad,” Dean stated.

Sam glowered. “You wouldn’t.”

“Try me.” Dean crumpled up the sandwich wrapper and tossed it lightly into the trash.

Sam stood up sharply and the chair made an uncomfortable rasping noise against the wood floor. “I’m going out.”  
Dean didn’t try and stop him, and when Sam slammed the door behind him, Dean had the feeling he’d screwed something up badly.

*

Sam didn’t speak to him for a few days. Well, he _spoke_ to Dean. Sam asked him about dinner, told him when he was going out, and helped Dean keep the room neat. But Sam didn’t ask Dean about his day, or offer any commentary about his. Sam didn’t proudly display good test grades or tease Dean about his porn collection. It was Dean’s job, both as the big brother and the one who screwed up, to fix the gap. But Dean just didn’t have the energy.

“I’m dating someone,” Sam finally told him.

Dean choked on his taco. “You’re _what_?”  
“Dating.” Sam neatly wiped up Dean’s spit up taco with a napkin.

Dean forced a smile. “Who’s the lucky girl?”

“No one.” Sam picked at his cuticle. “It’s a guy.”  
“Who?”  
Sam swallowed heavily. “James. I really like him, Dean. I like him _a lot_. I might even learn to love him. This guy… he gets me. He talks to me, and listens to my problems. James has been the friend I’ve always wanted, and the lover I’ve never had. I learn new things every day. I’m happy.”

Dean snorted. “Yeah, I bet he teaches you a lot of _new_ things.”

“I’m sorry, what the hell is that supposed to me?” Sam growled.

“You know how teenage boys are. The only thing on their mind is-,”  
“If you say sex, I’ll punch you.” Sam pushed aside his burrito. “My relationship with James is _way_ beyond sex. We kiss, a lot and it’s amazing, but I’m not sleeping with him. Not yet, that is.”

“You are not sleeping with that—with that _boy_ ,” Dean hissed. “Besides, we’re leaving soon. You won’t have time to develop a good relationship with him.”  
“We’ll do long distance,” Sam insisted confidently. “I’m falling in love with this guy, Dean. I’m gonna make it work.”

A possessive monster howled in Dean’s heart. Sam was _his_. Sam loved _Dean_. It was _Dean’s_ job to teach his baby brother about sex. Not that he knew a lot about gay sex. Just that it looked like it hurt a _lot_. Dean was willing to find out for Sam, though. “You. Will. Not. Make. This. Work. That’s my final word on it. Cut ties now before it’s too painful.”

Sam’s mouth dropped open. “I thought you’d be supportive! I know things are rough between us, but I thought you’d at least be happy that I’d found someone who makes me love myself. Turns out I was wrong.”

“Yeah, you were,” Dean agreed. “I’m looking out for your best interests.” The nagging voice in Dean said that he was only looking out for his own best interests, but Dean ignored it.

“What best interests? You want to make me miserable? Mission accomplished!” Sam’s eyes burned with rage. “You’re just like Dad, you know? You’re trying to control my life and take away anything that makes me feel normal or cheerful. You want to be Daddy’s good little minion? Nice work, Dean. You’re an ignorant bastard just like him.”   
Dean’s heart broke. “Sam-,”  
“No! All I’ve ever done is listen to you, Dean!” Sam was yelling now. “I’m listening to my heart this time. I don’t give two fucks if you say that’s cheesy or girly. I’m used to dad pushing me around. But _you_? I thought you would always be on my side! Guess I was wrong.” Sam stood and grabbed his coat. “You’re just a homophobic asshole who doesn’t love me.”

“That’s not tru-,”   
“I found someone that does love me. And I’m not giving up.” Sam twirled and slammed the door behind him. That was happening a lot lately, and Dean couldn’t chalk it up to teenage angst.

Sam’s words started to get through to him. Sam managed to exploit every single one of Dean’s insecurities. Daddy’s little soldier…unfeeling bastard…homophobic asshole. Dean bit his lip. Is that how he came off? The other stuff was true, Dean was definitely a fuck up. But homophobic? No! How could Dean be, if he was in love with another guy?

And that guy just happened to be his brother. Dean winced. He should be happy for Sam. He was in a healthy, loving relationship. And the more Dean thought about it, the more Dean heard homophobia in his words. How was Dean supposed to explain to Sam that he wasn’t a homophobe, he was just possessive of Sam because he was stupid enough to fall in love with the one person he could never have?

Dean sniffed and wiped at his eyes. He was too old to cry. But his brother, the person he loved more than anything in the world, had just punched Dean in the heart. Punched Dean in the heart, then pulled it out of his chest and stomped it into the ground. It was hard to keep the tears in.

Dean probably deserved it for being stupid enough to fall in incestuous love with the person he was supposed to _watch out for_. Not perv on. It was his one responsibility. And god, if John ever found out—he’d skin Dean alive. No. It hurt something awful to have Sam hating him the way he did, but at least Sam would be _safe_. He’d be safe from Dean’s creepy obsession and self-loathing. Dean hated James with every ounce of his body, but it was better that Sam be happy with him.

Sometimes protecting his baby brother hurt.

*

Dean sent dozens of texts and called Sam dozens of times. They rang until it reached voicemail, and Dean left angry, panicked messages until the little automatic voice said _voicemail full_. “Dammit Sam.”

A brief text came around midnight. _I’m fine. Stop calling. Not coming home_.

Relief and worry battled inside Dean. Relief that Sam hadn’t been taken by a monster, and worry because it was his job to keep Sam safe. If Sam was gone, then he was out of Dean’s control, and Dean _hated_ losing control.

Dean fired questions at Sam and called him again, but it went straight to voicemail. Sam had turned his phone off.

Dean took deep, calming breaths. Sam could take care of himself for a night. Dean would just be here in the motel, worrying his head off. He couldn’t even get drunk because if he were drunk or hungover when Sam needed him, Dean would never forgive himself.

Plus he’d lost his fake ID in Minnesota.

Dean tried to sleep but it was impossible without Sam’s nasal breathing beside him. He counted sheep, recited every city they’d visited backwards, and still all Dean could think about was Sam. Was he sleeping in James’ bed? Did they have sex? Dean hoped with all his heart they hadn’t. Sammy was his and his alone.

But it was this attitude that got Dean into this mess, now wasn’t it? Dean was overpossessive and he’d paid the price. Now Sam was angry with him.

“Come back, Sammy,” Dean whined into his pillow. “Sammy, Sam, please come back.”

Dean threw caution to the wind and dug around his dad’s duffle bag. He always kept some sort of alcohol in his bag for “injuries”. An unopened bottle of whiskey appeared at the bottom and Dean grabbed it. He could always replace it before John came home. Dean opened the alcohol and drank himself to sleep.  

*

Hangovers were the worst. His skull was splitting and he didn’t have Sam to get him aspirin and water and call him a baby. His mouth tasted like ash and werewolf guts. It was disgusting, and Dean missed his brother.

Dean threw up a couple of times, took some painkillers, and lay on the bed in nothing but his boxers. “Just kill me now,” Dean moaned. “It’ll be less painless this way.”

There was no one in the room to respond to his plea. The guns still lay on the table, partially clean. Sandwich wrappers and cookie boxes and empty coffee cups were littered around the room next to clipped newspaper columns. Everything about the room screamed of Dean and Sam. John was rarely home so his influence wasn’t showing through the two boys’ mess. “I miss you Sam.” Dean buried his face in his pillow. “Sammy.”

The room was quiet. James was probably making Sam laugh his beautiful laugh and he probably had his dimples out and everything. That was _Dean’s_ laugh; those were _Dean’s_ dimples. That was _Dean’s_ brother. James had no claim to him. Dean wished John would come home sooner and they could leave. He didn’t want to spend another second being around another guy who loved Sam. And worse, Sam loved him back. Dean wished there was more alcohol. It would be helpful. Or it would, at least, numb the pain.

There was a tiny click in the door and then the heavy wood slammed. Dean winced as the loud sound pounded against his ears. Whoever slammed the door was a cruel, cruel person with no sympathy for hangover. “Go ‘way.”

“I live here too, fucker.” A shoe hit Dean’s back. “Oops.”   
“Still mad, Sammy?” Dean squished into the pillow. Hm. Soft. He needed something to drink. Juice. And more painkillers.

“I don’t want to talk to you, homophobe.” Sam’s other shoe hit something hard, leaving a thud in its wake.

“’M not a homophobe,” Dean protested. “How can I be?”  
“Well, you insulted and belittled me because I’m dating a guy,” Sam snarled.

“No,” Dean groaned. “No, Sammy. S’not—s’not it. Gimme a chance to explain.”  
“Maybe if you weren’t so hungover we could have a normal conversation, you drunk.”   
Dean winced. It hurt, but Sam was angry. He forced himself to sit up and look at his brother. “Okay. I can have this conversation.”   
“Fine. Now talk. Explain why you were such a douchebag last night when all I wanted to do was spend time with my _boy_ friend.” Sam crossed his arms and watched Dean petulantly. He never looked more like the 16-year-old kid than he did now.

“I was-,” Dean stopped. “I’m protective,” Dean said slowly. “Not having you around makes me edgy. And this guy was pulling you away.”  
“So what?” Sam snapped. “You got overprotective, as usual? Are you mad at James, Dean, because I spend time with him! I’d spend time with you, too, if you stopped being Dad’s perfect little minion. So drop the whole possessive, jealous act.” Dean didn’t say anything and Sam’s eyes widened. “Seriously? You’re _jealous_? Of my boyfriend?” Dean shrugged. Sam let out a short, humorless laugh. “Even for you, that’s pathetic.”

Dean’s lungs were too big. There wasn’t enough air to fill them up. “I…” He didn’t really have a good excuse, so he rolled back onto his side with his back facing Sam.

The room lapsed into silence again. A few minutes passed and then Dean felt a wide palm on his shoulder. “You’re not pathetic,” Sam muttered. “Sorry.”  
“No, I am,” Dean protested. “I’m disgusting and wrong and you shouldn’t even be around me.”

“Dean, what are you talking about?” Sam asked incredulously. “It’s just a little jealousy. It’s normal.”

“Not this kind,” Dean said helplessly.

“What _kind_?” Sam pushed. “Dean, you’re confusing me.”  
Do it fast, like ripping off a band-aid. “I love you.”  
Sam’s expression didn’t change. “Well yeah, I love you too. That doesn’t mean you can be nasty because of who I lov-,”  
“No!” Dean exclaimed. “You don’t _get_ it. I _love_ you. I love you like you love James. That’s why I’m pathetic and disgusting and wrong.”

Sam let out a heavy sigh. “Wow.”

Dean didn’t respond. What could someone say after they confessed their incestuous love to their innocent, baby brother?

“Dean, look at me,” Sam said gently. The tone had none of the contempt Dean expected to here. His brother was always too forgiving.

“Dean, I’m not upset,” Sam murmured.

Dean rolled to face him. “What?”   
Sam helped Dean sit up and took his hand. “I’m not mad, or disgusted, or any other horrible situation that you’re imagining in your head. I know you do that, Dean.”

“But-,”   
“The only thing I’m mad about,” Sam interrupted. “Is that you let me live _16 years_ before telling me. You let me think _I_ was disgusting for loving you instead of telling me.”

Dean stared at Sam. It was a lot to take it at once, but he kept coming back to the fact that Sam didn’t hate him, Sam _loved_ him, loved Dean like Dean loved Sam. “But…James?”  
Sam snorted. “I showed up and he had his cock down another guy’s throat.”   
Dean’s blood boiled. “I’ll kill him.”

“Please don’t,” Sam said. “He’s not worth the effort.” He smacked Dean’s head. “That’s for not telling me.”   
“How was I supposed to know that you felt that way? You could have told me!”

Sam rolled his eyes. “Insecure little brother, here! And besides, I’m pretty sure following you around and my complete lack of any relationships _ever_ was a good sign.”

“James,” Dean pointed out.

Sam shrugged. “I figured you weren’t interested, and I was sick of waiting.”

Dean pulled Sam into his arms. “I’m sorry I ever made you wait.”   
“You can make it up to me.” Sam pushed Dean onto his back. Sam was 4 years younger, but almost taller than Dean and strong enough to manhandle him. It made Dean’s dick twitch excitedly; Sam holding him down and fucking him wasn’t an uncommon fantasy of Dean’s, just an incredibly tabooed one.

“Fine, grumpy.” Dean smirked up at Sam. “What’d you have in mind, big talker?”

Sam sat back on his haunches. “I want you to be quiet, for one. You can keep your mouth closed for a few hours, can’t you?”  
“ _Hours?”_ Dean spluttered. “No—I can’t— _hours?”_

“I can gag you,” Sam suggested. “I’m already going to tie you up.”   
“Oh really?” Dean narrowed his eyes. “Who says I’m going to let you?” He pushed Sam off and managed to kneel on the bed before Sam’s hulking weight was slamming into his and pinning him on the bed.

“Who says I need you to _let me_?” Sam whispered. Dean tugged on his wrists but Sam kept them trapped firmly above his head. “You’re going to stay when I let go of your arms, and you’re not going to fight when I get the handcuffs to keep them there. Understand?”

Dean glared at his brother. Sam’s smirk only grew, so Dean knew he hadn’t disguised the lust very well. “I hate you.”

“Yeah, sure you do. Now stay,” Sam ordered. Dean’s body stilled but his eyes wandered with Sam. Sam definitely bent over slower than was necessary. Tease.

“Hurry your ass up,” Dean growled.

“Bossy.” Sam teased.

“I’m going to get the lube. Take your clothes off while I find it.”

Dean glared. “Why do you have lube?”  
Sam gave him an exasperated look. “Relax, will you? It’s unopened.” Dean kept his eyes firmly on Sam’s ass while he moved around to find the lube. He started to peel off his clothes and threw them on his brother. Sam growled when the snap of his jeans hit his head. The younger Winchester started to strip his own clothes off, hopping out of his jeans while trying to find the lube. With a cry of triumph, Sam held up the small tube and crawled back onto the bed. Dean’s skin goosebumped from the cold air but Sam’s warm skin soothed the chill.

Dean felt Sam’s thick cock against his thigh. His little brother was proportional and oh, Dean was definitely _not_ that big when he was 16. And now that giant cock was going up his ass. “Oh, fuck,” Dean groaned. _It’s not going to fit, it’s going to hurt._

“Shh, it’s gonna be okay.” Sam leaned down and kissed Dean. He hadn’t realized he was talking aloud. “I’m gonna make it good for you, big brother.”

“I’ve never done this before,” Dean whispered.

“Good, I get to be your first.” Sam leaned down and kissed Dean.

Dean lost himself against Sam’s lips, but pulled away with a gasp when he felt a slick finger pressing against his hole. “Sam!”

“Relax. It will be easier if you relax, Dean,” Sam instructed. “It’s gonna be okay.”

Dean didn’t believe him. Sam was huge, and Dean had never had _anything_ up his ass before. “You gotta trust me,” Sam insisted. His eyes watched Dean earnestly.

“I trust you.” Dean forced his muscles to relax and Sam added another finger. He had plenty of lube on his fingers so the fingers scissored him open easily. It stung a little bit, but Sam crooked his finger and it hit something that felt _really_ good. “Fuck, Sam!”

“Found it,” Sam muttered under his breath. Sam had three fingers inside Dean and prodded against that wonderful spot every time.

“Fuck me,” Dean moaned. “Sam, fuck me!”

“Are you sure? Maybe I should stretch you more-,”   
“Seriously, get your dick in my ass,” Dean demanded. “Or I’m gonna come like this.”

Sam removed his fingers. “Lemme grab a condom.”   
“I’m clean, I’ve been tested.” Dean gritted. “You’re clean, because you’re a fucking virgin.” Dean’s eyes narrowed. “You _are_ a virgin, right?”   
“Yes, possessive bastard.” Sam dropped the condom and slicked up his cock. “Keep taking deep breaths for me, okay Dean?”

Dean nodded and breathed steadily. He closed his eyes and adjusted his handcuffed arms. Something huge—Sam’s cock—pressed against his ass and started to slide in. “Fuck,” Dean grunted. It _hurt_. His erection started to wilt.

“I’m sorry, I’m sorry,” Sam repeated. He froze in place until Dean growled.

“I’m not a girl.” Dean glared until Sam continued to push in. It hurt like a bitch and Dean was only half hard at this point. It felt like hours until Sam was finally pressed balls against his ass.

Sam’s strong hand wrapped around Dean’s cock and started to stroke it. Sam’s hands were surprisingly soft and blood returned to his cock until Dean was fully hard again. Sam modified his position until Sam’s cock was pressing against Dean’s prostate. “You can move,” Dean said. “Go ahead.”

“Are you sure? I can wait.” Sam’s innocent teenage eyes watched carefully with ill-disguised lust.

“Just _move_!”

Sam pulled out slowly and pushed back in, hitting Dean’s prostate again. He picked up the rhythm until Dean was writhing and pulling desperately at his handcuffs. “Sam, Sam, fuck!”  
“That’s the intention.” Sam’s fingers played with Dean’s nipples and he keened. One of Dean’s old girlfriend’s stroked across his nipples once and he discovered exactly how sensitive they are. He pushed his chest into Sam’s fingers. “Sensitive nipples, huh?”  
“Oh, god,” Dean moaned. “Yes! It feels so good!”

Sam grinned evilly. “Good.”

Sam’s thrusts slowed just as Dean felt like he could come. “Sam,” Dean whined. “Not fair.”   
“I’m not trying to be fair.” Sam smirked and before Dean knew it, his lips were around Dean’s nipple. His tongue lapped at the sensitive nub and Dean cried out in pleasure.

“You are _way_ too evil for a 16 year old teenager,” Dean groaned. “Are you sure you’re a virgin?”  
“I’ve been saving myself,” Sam purred. “You were well worth the wait.” He rolled his hips and Dean bucked.

“Make me come,” Dean begged. “Please, please, I need to come!” His cock steadily leaked precome. Sam’s hand reached around Dean’s cock and stroked up and down, using the precome to slick the way. Sam kept Dean on the edge, the older Winchester, pleading to come.

“Only because I’m such a good big brother,” Sam whispered. “I’m gonna let you come.” He kept jerking Dean off until his orgasm exploded out of him. Come splattered on Dean’s chest and Sam’s thrusts stuttered. “Dean!” He pushed in and came inside Dean.

When they came down from their high, Sam carefully slid out of Dean. His come leaked out and dripped down Dean’s thighs. “I’ll get a washcloth,” Sam offered.

“I’ll be here,” Dean mumbled sleepily. He barely felt the warm fabric clean him up or Sam’s warm arms wrap around him under the covers. “Should have known you’d be a cuddler.”   
“Shut up and sleep,” Sam yawned. “I love you.”   
“Love you too, Sammy.” Dean slid his hand into Sam’s. “Love you too.”

  

**Author's Note:**

> if you want a kink/prompt written, comment on one of my stories!


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